Harry Sinden had his heart set on a defenceman when the Boston Bruins had the eighth pick in the 1979 NHL entry draft.

Realistically, he figured he had no shot at Rob Ramage, who was going first to Colorado, or Craig Hartsburg, who would be gone before the Bruins would choose. The player he really coveted: Keith Brown of the Portland Winter Hawks.

But when the Chicago Blackhawks used the seventh pick in the draft to select Brown, the Bruins did what all fine hockey operations do when matters don’t go their way: They panicked.

They called a time out. They yelled and screamed just a little. And they went back to the draft list of chief scout Gary Darling and moved on to the next name.

And when time ran out, they announced through gritted teeth they had selected, against their better judgment, from the Sorel Blackhawks of the Quebec Major Junior League of all places, Raymond Bourque.

“Sometimes in life and in hockey, you’re better off to be lucky than smart,” said Jimmy Devellano, the Hall of Fame executive with the Detroit Red Wings. “From my 45 years in the NHL, I can tell you, yes, you’ve got to be prepared. Yes, you’ve got to do your homework. Yes, you’ve got to have good scouts. Yes, all those things are vital and important, but believe me, when you’re talking about 18-year-old kids, boy does it ever pay to get lucky.”

Devellano articulates this better than most. In 1977, he was the chief scout for the New York Islanders. The Isles had the 15th pick in the entry draft. When it came for them to choose, he wasn’t certain which way to go.

“We really had a tough decision to make,” said Devellano. “It seems laughable today but we had to pick between Mike Bossy and Dwight Foster. You can say, what the hell kind of decision was that to make? But you have to remember, Dwight Foster had a led a tougher league in scoring (OHL). Bossy led the Quebec League in scoring, which was a softer non checking league. We made the pick but we weren’t sure about it. Foster went next to Boston. We got lucky.”

That summer, Devellano and Darling and a group of NHL scouts happened to get together to go to a Blue Jays game. Before the game, Darling gave Devellano a mock hug and said: “Thanks for leaving Foster for us.”

It was the last time he would thank Devellano for anything.

“Luck,” said Devellano. Sometimes luck. Sometimes smarts. Often good fortune. The NHL draft can be all of those things. But when generational players such as Bossy and Bourque end up as accidental choices, well, you realize what a game of cards is all is: And often you can’t control your hand.

In 1983, Devellano’s first season with the Red Wings, Detroit had fourth pick in the draft. The Minnesota North Stars had first pick.

“We had three players we really liked, Pat LaFontaine, Steve Yzerman and Sylvain Turgeon. Our worry was, picking fourth, we might not get any of them,” Devellano said.

The North Stars had rated LaFontaine, Yzerman and Brian Lawton among their top three and administered trend-setting psychological tests to all three teenagers. Lawton’s score blew the other two away. With the first pick in the ’83 draft, the North Stars chose Lawton.

“We knew then we were going to get one of the three players we liked,” said Devellano.

But the player he coveted most was LaFontaine.

“Pat LaFontaine grew up in Detroit, played minor hockey in Detroit and when I arrived in Detroit we only had 2,100 season ticket holders,” he explained. “We were in worse shape than the Phoenix Coyotes at the gate, We needed Pat. He would have been a real marquee guy for our franchise. When the Islanders picked LaFontaine third (Sylvain Turgeon had gone second to Hartford), we were disappointed, I mean really disappointed. We thought we needed LaFontaine for so many reasons.

“We knew Steve Yzerman was a pretty good player.” They didn’t know, like Bossy and Bourque, he too, was generational.

“We’ve had lots of luck over the years. Ken Holland would the first to tell you that. Getting Pavel Datsyuk where we got him (171st overall, 1998) oh boy were we lucky. Getting Henrik Zetterberg where we got him (210th pick, 1999) boy were we lucky. Getting a top four defenceman like Jonathan Eriksson with the last pick of the draft (291st in 2002), boy were we lucky.”

The Maple Leafs are set to pick fifth on Friday night in Pittsburgh. The last time they picked that high, they traded up to select Luke Schenn. Two of the next three defencemen taken were Tyler Myers and Erik Karlsson.

This is the NHL draft: Historically, some teams have had dumb luck, some teams have just been dumb.

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